The aurachin C monooxygenase from the bacterium Stigmatella aurantiaca accepts both NADH and NADPH as cofactor, but has a preference for NADH. It catalyses the initial steps in the conversion of aurachin C to aurachin B. The FAD-dependent monooxygenase catalyses the epoxidation of the C2-C3 double bond of aurachin C, which is followed by a semipinacol rearrangement, causing migration of the farnesyl group from C3 to C4.
The aurachin C monooxygenase from the bacterium Stigmatella aurantiaca accepts both NADH and NADPH as cofactor, but has a preference for NADH. It catalyses the initial steps in the conversion of aurachin C to aurachin B. The FAD-dependent monooxygenase catalyses the epoxidation of the C2-C3 double bond of aurachin C, which is followed by a semipinacol rearrangement, causing migration of the farnesyl group from C3 to C4.
during the AuaG-catalysed transformation, the transient C2-C3 epoxide can be formed and opened to the tertiary alcoholate. The ether product is supposed to arise from rapid retro-[2,3]-Wittig rearrangement assisted by the presence of both carbonyl and iminium functions
formation of aurachin B requires the presence of AuaH. AuaG and AuaH act sequentially and conversion of aurachin C into aurachin B occurs by oxidation and subsequent reduction
AuaG is able to oxidize short-chain analogues of aurachin D. A retro-[2,3]-Wittig rearrangement is observed with isoprenyl substrate analogues. Saturated-chain analogues of N-oxidized aurachin C are not transformed by the C3 to C4 semipinacol reaction
AuaG performs epoxidation of the C2-C3 bond of aurachin C. The resulting epoxide is opened, thereby resulting in the imine N-oxide and the alpha-keto tertiary alcoholate
first step in the conversion of aurachin C to aurachin. The FAD-dependent monooxygenase catalyses the epoxidation of the C2-C3 double bond of aurachin C, this is followed by a semipinacol rearrangement, causing migration of the farnesyl group from C3 to C4
binuclear iron monooxygenase gene cluster MimABCD plays essential roles in propane and acetone metabolism. A MimA deletion mutant has lost the ability to grow on propane, acetone or methylethylketone as source of carbon and energy
binuclear iron monooxygenase gene cluster MimABCD plays essential roles in propane and acetone metabolism. A MimA deletion mutant has lost the ability to grow on propane, acetone or methylethylketone as source of carbon and energy
binuclear iron monooxygenase gene cluster MimABCD plays essential roles in propane and acetone metabolism. A MimA deletion mutant has lost the ability to grow on propane, acetone or methylethylketone as source of carbon and energy
binuclear iron monooxygenase gene cluster MimABCD plays essential roles in propane and acetone metabolism. A MimA deletion mutant has lost the ability to grow on propane, acetone or methylethylketone as source of carbon and energy
Furuya, T.; Hirose, S.; Osanai, H.; Semba, H.; Kino, K.
Identification of the monooxygenase gene clusters responsible for the regioselective oxidation of phenol to hydroquinone in mycobacteria
Appl. Environ. Microbiol.
77
1214-1220
2011
Mycolicibacterium smegmatis (A0QTU8), Mycolicibacterium goodii (E9RFS9 and E9RFT0 and E9RFT1 and E9RFT2), Mycolicibacterium goodii 12523 (E9RFS9 and E9RFT0 and E9RFT1 and E9RFT2), Mycolicibacterium smegmatis ATCC 700084 (A0QTU8)
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Enzyme Nomenclature
1.14.13.222 aurachin C monooxygenase/isomerase
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